Bifunctional thiourea-based organocatalyst promoted kinetic resolution polymerization of racemic lactide to isotactic polylactide

Jiang Dai; Wei Xiong; Dong-Yu Li; Zhongzheng Cai; Jian-Bo Zhu

doi:10.1039/d3cc04203k

Bifunctional thiourea-based organocatalyst promoted kinetic resolution polymerization of racemic lactide to isotactic polylactide

Chem Commun (Camb). 2023 Oct 24;59(85):12731-12734. doi: 10.1039/d3cc04203k.

Authors

Jiang Dai¹, Wei Xiong¹, Dong-Yu Li¹, Zhongzheng Cai¹, Jian-Bo Zhu¹

Affiliation

¹ National Engineering Laboratory of Eco-Friendly Polymeric Materials (Sichuan), College of Chemistry, Sichuan University, Chengdu 610064, People's Republic of China. zzcai@scu.edu.cn.

PMID: 37800444
DOI: 10.1039/d3cc04203k

Abstract

Here, we prepared a series of thiourea-based organocatalysts 1-7 by combining two stereogenic elements: binaphthyl-amine and cyclohexyl diamine moieties. Catalyst (R,S)-1 facilitated a stereoselective polymerization of rac-LA to afford iso-enriched PDLA with P_m of 0.96 while its enantiomer (S,R)-1 produced PLLA with P_m of 0.96. These iso-enriched PLA contributed to forming a stereocomplexed PLA with a significantly increased T_m of 196 °C.